Maleic Anhydride → N-(3-hydroxyphenyl)maleimide

Participants

Reaction Conditions

Reaction Steps

A 54.57 gram portion of m-aminophenol (0.50 mole) and 1000 milliliters of acetic acid were added to a reactor and maintained under a nitrogen atmosphere with stirring. The stirred solution was maintained at 25° C., then 49.03 grams of maleic anhydride (0.50 mole) dissolved in 100 milliliters of acetic acid was added to the reactor and heating to 115° C. commenced. The 115° C. reaction temperature was maintained for 18 hours (64,800 s), then the product was dried under vacuum by rotary evaporation at 120° C. for 30 minutes (1800 s) to a dark brown solid. The crude product was extracted with two 250 milliliter portions of o-dichlorobenzene at 120° C. The combined extracts were maintained at 2° C. for 24 hours (86,400 s) then the light yellow orange colored crystalline product was recovered by filtration and dried under vacuum at 60° C. for 24 hours (86,400 s) to provide 23.1 grams of N-(3-hydroxyphenyl)maleimide. Infrared spectrophotometric analysis of a film sample, nuclear magnetic resonance spectroscopy and mass spectroscopy (m/Z=214) all confirmed the product structure.

Provenance & Evidence